4-Methylmorpholine → ((5-Isoxazolyl)methyl)-(4-nitrophenyl)carbonate

HRID 52844Notes

Reaction equation

HRID 52844 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][C:9](Cl)=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:14][CH2:15][C:16]1[O:20][N:19]=[CH:18][CH:17]=1.CN1CCOCC1>C(Cl)Cl>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][C:9]([O:14][CH2:15][C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 129050981,2-Oxazol-5-ylmethanol

Product 1

HCID 18939817((5-Isoxazolyl)methyl)-(4-nitrophenyl)carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 631 mg (2.65 mmol) sample of p-nitrophenoxycarbonylchloride in 2 mL of methylene chloride was added to a solution of 310 mg (3.13 mmol) of 5-hydroxymethyisoxazole and 0.344 mL of 4-methylmorpholine in 2 mL of methylene chloride cooled in an ice bath. The solution was stirred for 4 hours. The mixture was diluted with methylene chloride, which was washed with water, dried and concentrated. The crude product was chromatographed on silica gel, eluting with 2% ethyl acetate in methylene chloride. The solvent was removed and the product dried to afford 0.473 g of the title compound, which was taken directly to the next step.

Workup

  1. temperaturecooled in an ice bath
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel
  6. washeluting with 2% ethyl acetate in methylene chloride
  7. customThe solvent was removed
  8. customthe product dried

Sources & evidence

ORD record
ord-45bff5541a6445968c497a9102844961
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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